WO2007019719A1 - Cooling compounds - Google Patents
Cooling compounds Download PDFInfo
- Publication number
- WO2007019719A1 WO2007019719A1 PCT/CH2006/000427 CH2006000427W WO2007019719A1 WO 2007019719 A1 WO2007019719 A1 WO 2007019719A1 CH 2006000427 W CH2006000427 W CH 2006000427W WO 2007019719 A1 WO2007019719 A1 WO 2007019719A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- isopropyl
- compounds
- carbons
- branched alkyl
- Prior art date
Links
- 0 C*(C)CNC(C(*)(*)*)=O Chemical compound C*(C)CNC(C(*)(*)*)=O 0.000 description 1
- RDOAUPPSCNSYPM-UHFFFAOYSA-N C1C=CN=CC1 Chemical compound C1C=CN=CC1 RDOAUPPSCNSYPM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/40—Acylated substituent nitrogen atom
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
- A23L2/52—Adding ingredients
- A23L2/56—Flavouring or bittering agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
- A61K2800/24—Thermal properties
- A61K2800/244—Endothermic; Cooling; Cooling sensation
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
- A61K2800/92—Oral administration
Definitions
- This invention relates to cooling compounds.
- Cooling compounds that is, chemical compounds that impart a cooling sensation to the skin or the mucous membranes of the body, are well known to the art and are widely used in a variety of products such as foodstuffs, tobacco products, beverages, dentifrices, mouthwashes and toiletries.
- X, Y and Z are selected independently from the group consisting of H, halogen, OH, Me, Et, MeO and EtO, and R 1 , R 2 and R 3 together comprise at least 6 carbons, selected such that
- R 1 is selected from the group consisting of H, Me, Et, isopropyl and
- R and R are independently selected from the group consisting of Me. Et, isopropyl and C 4 -branched alkyl; or
- BESTATIGUNGSKOPIE any two or all of R 1 , R 2 and R 3 together form a monocyclic, bicyclic or tricyclic radical having up to 10 carbons.
- Me is defined as methyl
- Et is defined as ethyl
- Examples of cyclic radicals as described under (b) above include 3-para-menthyl, bornyl and adamantyl.
- the compounds of formula (I) may comprise one or more chiral centres and as such may exist as a mixture of stereoisomers, or they may be resolved as isomerically pure forms. Resolving stereoisomers adds to the complexity of manufacture and purification of these compounds and so it is preferred to use the compounds as mixtures of their stereoisomers simply for economic reasons. However, if it is desired to prepare individual stereoisomers, this may be achieved according to methods known in the art, e.g. preparative HPLC and GC or by stereoselective syntheses.
- the compounds are those in which X, Y, Z are H, OH, Me or OMe. In certain embodiments, the compounds are those in which m is 2; X, Y and Z are H or Me and R 1 , R 2 and R 3 are taken from Table 1.
- Table 1 Exemplary R , R and R groups.
- a particularly effective compound is that in which R 1 is H and R 2 and R 3 together form a 3-p-menthyl ring.
- Examples of effective compounds are (lR,2S,5R)-2-isopropyl-5-methyl-N- (pyridinalkyl)cyclohexanecarboxamide and (2S,5R)-2-isopropyl-5-methyl-N- (pyridinalkyl)cyclohexanecarboxamide.
- a compound is also provided according to formula I as hereinabove described, in which X, Y, Z, R 1 are H and R 2 , R 3 have the meanings given hereinabove.
- R 1 is hydrogen and R 2 and R 3 are independently selected from the group consisting of Me, Et and C 3 -C 4 branched alkyl; or R 1 , R 2 and R 3 together form a monocyclic, bicyclic or tricyclic radical having up to 10 carbons.
- the compounds may be easily prepared and isolated by art-recognized methods
- the compounds may be used in products that are applied to the mouth or the skin to give a cooling sensation.
- applying is meant any form of bringing into contact, for example, oral ingestion or, in the case of tobacco products, inhalation, hi the case of application to the skin, it may be, for example, by including the compound in a cream or salve, or in a sprayable composition.
- the range of products in which the compounds may be used is very wide, and it includes by way of example only, dentifrices such as toothpaste and toothgel, mouthwashes, foodstuffs, beverages, confectionery, tobacco products, skin creams and ointments, both cosmetic and medicinal.
- the compounds may be used alone or in combination with other cooling compounds known in the art, e.g., menthol, menthone, isopulegol, N-ethyl p- menthanecarboxamide (WS-3), N,2,3-trimethyl-2-isopropylbutanamide (WS-23), menthyl lactate (FrescolatTM ML), menthone glycerine acetal (FrescolatTM MGA), mono-menthyl succinate (PhyscoolTM), mono-menthyl glutarate, O-menthyl glycerine (Cool ActTM 10), menthyl-N,N-dimethylsuccinamate and 2-sec-butylcyclohexanone (FreskomentheTM).
- other cooling compounds known in the art, e.g., menthol, menthone, isopulegol, N-ethyl p- menthanecarboxamide (WS-3), N,2,3-tri
- Peppermint oil Terpeneless 0.300 g
- PluronicTM F127 nonionic surfactant 5.000 g Sodium Saccharin 0.600 g
- the chemicals are mixed in the toothgel, a piece of toothgel is put on a toothbrush and a panelist's teeth are brushed.
- the mouth is rinsed with water and the water is spit out. An intense cooling sensation is felt by the panelist in all areas of the mouth.
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- Epidemiology (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Birds (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Medicinal Preparation (AREA)
- Fats And Perfumes (AREA)
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US11/990,103 US9452982B2 (en) | 2005-08-15 | 2006-08-14 | Pyridinyl cyclohexanecarboxamide cooling compounds |
ES06761278.8T ES2668361T3 (es) | 2005-08-15 | 2006-08-14 | Compuestos refrigerantes |
JP2008526348A JP5383191B2 (ja) | 2005-08-15 | 2006-08-14 | 清涼化合物 |
EP06761278.8A EP1917074B1 (en) | 2005-08-15 | 2006-08-14 | Cooling compounds |
BRPI0616821-3A BRPI0616821B1 (pt) | 2005-08-15 | 2006-08-14 | Método para proporcionar um efeito refrescante em um produto e produto possuindo um efeito refrescante |
CN200680029790XA CN101257949B (zh) | 2005-08-15 | 2006-08-14 | 清凉化合物 |
US15/276,248 US10221136B2 (en) | 2005-08-15 | 2016-09-26 | Pyridinyl cyclohexanecarboxamide cooling compounds |
US16/290,300 US11059783B2 (en) | 2005-08-15 | 2019-03-01 | Pyridinyl cyclohexanecarboxamide cooling compounds |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US70815305P | 2005-08-15 | 2005-08-15 | |
US60/708,153 | 2005-08-15 |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US11/990,103 A-371-Of-International US9452982B2 (en) | 2005-08-15 | 2006-08-14 | Pyridinyl cyclohexanecarboxamide cooling compounds |
US15/276,248 Continuation US10221136B2 (en) | 2005-08-15 | 2016-09-26 | Pyridinyl cyclohexanecarboxamide cooling compounds |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2007019719A1 true WO2007019719A1 (en) | 2007-02-22 |
Family
ID=37215970
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/CH2006/000427 WO2007019719A1 (en) | 2005-08-15 | 2006-08-14 | Cooling compounds |
Country Status (7)
Country | Link |
---|---|
US (3) | US9452982B2 (zh) |
EP (1) | EP1917074B1 (zh) |
JP (1) | JP5383191B2 (zh) |
CN (1) | CN101257949B (zh) |
BR (1) | BRPI0616821B1 (zh) |
ES (1) | ES2668361T3 (zh) |
WO (1) | WO2007019719A1 (zh) |
Cited By (30)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2008107137A2 (en) * | 2007-03-02 | 2008-09-12 | Givaudan Nederland Services B.V. | Compositions comprising a physiological coolant |
WO2008141469A2 (en) * | 2007-05-23 | 2008-11-27 | Givaudan Sa | Butone derivatives useful as cooling agents |
WO2008148234A1 (en) | 2007-06-06 | 2008-12-11 | Givaudan Sa | Salt enhancement |
WO2008151460A2 (en) | 2007-06-13 | 2008-12-18 | Givaudan Sa | Cooling compounds |
WO2009012609A1 (en) | 2007-07-23 | 2009-01-29 | Givaudan Sa | Amide addition reaction |
WO2009115165A2 (de) * | 2008-03-20 | 2009-09-24 | Beiersdorf Ag | Kühlende zubereitungen für den humanen haut- und/oder schleimhautkontakt mit einem gehalt an (1r,2s,5r)-2-isopropyl-5-methyl-n-(2-(pyridin-2-yl)ethyl-cyclohexancarboxamid und/oder (1r,2s,5r)-n-(4-(cyanomethyl)-phenyl)-2-isopropyl-5-methylcyclohexancarboxamid |
WO2009115164A2 (de) * | 2008-03-20 | 2009-09-24 | Beiersdorf Ag | Kühlende kosmetische oder dermatologische zubereitungen mit einem gehalt an (1r,2s,5r)-2-isopropyl-5-methyl-n-(2-(pyridyn-2-yl)ethyl-cyclohexancarboxamid und/oder (1r,2s,5r)-n-(4-(cyanomethyl)phenyl)-2-isopropyl-5- methylcyclohexancarboxamid mit menthoxypropandiol |
WO2009115163A2 (de) * | 2008-03-20 | 2009-09-24 | Beiersdorf Ag | Kühlende kosmetische oder dermatologische zubereitungen mit einem gehalt an (1r,2s,5r)-2-isopropyl-5-methyl-n-(2-(pyridyn-2-yl)ethyl-cyclohexancarboxamid und/oder (1r,2s,5r)-n-(4-(cyanomethyl)phenyl)-2-isopropyl-5- methylcyclohexancarboxamid zu reduktion von hautrötungen |
WO2009127282A1 (de) * | 2008-03-20 | 2009-10-22 | Beiersdorf Ag | Zubereitungen zur verringerung von juckreiz und anderen missempfindungen mit (1 r,2s,5r)-isopropyl-5-methyl-n(2-(pyridin-2yl)ethyl- cyclohexancarboxamid und/oder (1r,2s,5r)-n-(4-(cyanomethyl)-phenyl)-2- isopropyl-5-methylcyclohexancarboxamid |
WO2009140783A1 (en) * | 2008-05-22 | 2009-11-26 | Givaudan Sa | Cooling composition |
WO2010076123A2 (en) | 2008-12-30 | 2010-07-08 | Unilever Nv | A non-freezing dentifrice composition |
WO2010128026A2 (en) * | 2009-05-05 | 2010-11-11 | Givaudan Sa | Organic compounds |
WO2010149798A2 (en) | 2010-06-14 | 2010-12-29 | Symrise Ag | Use of polyols for enhancing the cooling effect of a cooling substance and cooling mixtures having an enhanced cooling effect |
WO2011012421A1 (en) | 2009-07-29 | 2011-02-03 | Unilever Nv | A dentifrice composition comprising polyethyleneglycol and a cooling agent |
WO2011012671A1 (en) | 2009-07-29 | 2011-02-03 | Givaudan Sa | Improvements in or relating to organic compounds |
WO2011061330A2 (de) | 2009-11-20 | 2011-05-26 | Symrise Ag | Verwendung physiologischer kühlwirkstoffe und mittel enthaltend solche wirkstoffe |
WO2012113873A2 (en) | 2011-02-23 | 2012-08-30 | Givaudan Sa | Organic compounds |
US8309598B2 (en) | 2007-12-19 | 2012-11-13 | Givaudan S.A. | Cooling compounds |
US8357318B2 (en) | 2007-05-08 | 2013-01-22 | Givaudan S.A. | Wax encapsulation |
WO2013014235A2 (en) | 2011-07-26 | 2013-01-31 | Givaudan Sa | Rinse-off compositions |
US8377422B2 (en) | 2007-12-07 | 2013-02-19 | Givaudan S.A. | Carboxamide derivatives having cooling properties |
WO2013041621A1 (de) | 2011-09-20 | 2013-03-28 | Basf Se | Niedermolekulare modulatoren des kälte-menthol-rezeptors trpm8 und deren verwendung |
USRE44339E1 (en) | 2003-11-21 | 2013-07-02 | Givaudan S.A. | N-substituted P-menthane carboxamides |
US8710096B2 (en) | 2008-08-26 | 2014-04-29 | Basf Se | Detection and use of low molecular-weight modulators of the cold-menthol receptor TRPM8 |
US9029415B2 (en) | 2010-06-14 | 2015-05-12 | Symrise Ag | Cooling mixtures with an enhanced cooling effect of 5-methyl-2-(propane-2-yl)cyclohexyl-N-ethyloxamate |
WO2019043164A1 (de) | 2017-08-31 | 2019-03-07 | Basf Se | Verwendung physiologischer kühlwirkstoffe und mittel enthaltend solche wirkstoffe |
EP3689324A1 (de) | 2019-02-04 | 2020-08-05 | Symrise AG | Neue kühlstoffe und zubereitungen, die diese enthalten |
WO2022105986A1 (de) | 2020-11-17 | 2022-05-27 | Symrise Ag | Neue kühlstoffe und zubereitungen, die diese enthalten |
WO2022207944A2 (en) | 2022-07-11 | 2022-10-06 | Symrise Ag | Novel mixtures and uses of (2e)-3-(1,3-benzodioxol-5-yl)-n-phenyl-n-(tetrahydro-3-furanyl)-2-propenamide |
WO2023144326A1 (de) | 2022-01-28 | 2023-08-03 | Symrise Ag | Neue kühlstoffe und zubereitungen, die diese enthalten |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BR112018006471B1 (pt) | 2015-10-01 | 2024-02-27 | Senomyx, Inc | Composto, composição, método de modular o membro de melastina do canal potencial do receptor transitório 8 (trpm8), método de modular a sensação de resfrescância de uma composição e método de induzir uma sensação de refrescância em um ser humano ou animal |
EP3509641A1 (en) | 2016-09-12 | 2019-07-17 | ST IP Holding AG | Formulations of 4-methyl-5-(pyrazin-2-yl)-3h-1.2-dithiole-3-thione, taste-modified formulations, and methods of making and using same |
JP2019531344A (ja) | 2016-09-12 | 2019-10-31 | エスティー アイピー ホールディング エージー | 4−メチル−5−(ピラジン−2−イル)−3h−1,2−ジチオール−3−チオンの処方物、ならびにそれらの製造方法及び使用方法 |
JP2018203645A (ja) * | 2017-05-31 | 2018-12-27 | ライオン株式会社 | 口腔用組成物 |
EP3806661A1 (en) | 2018-08-10 | 2021-04-21 | Firmenich Incorporated | Antagonists of t2r54 and compositions and uses thereof |
JP2020070263A (ja) * | 2018-11-01 | 2020-05-07 | ライオン株式会社 | 液体口腔用組成物 |
US11135220B1 (en) | 2020-04-08 | 2021-10-05 | St Ip Holding Ag | Methods of treating viral infections with formulated compositions comprising 4-methyl-5-(pyrazin-2-yl)-3H-1,2-dithiole-3-thione |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH491111A (de) * | 1966-01-28 | 1970-05-31 | Geigy Ag J R | Verfahren zur Herstellung von neuen Amiden aliphatischer Carbonsäuren |
DE2458562A1 (de) * | 1973-12-12 | 1975-06-19 | Wilkinson Sword Ltd | Verbrauchsprodukt mit physiologischer kuehlwirkung |
US4150052A (en) * | 1971-02-04 | 1979-04-17 | Wilkinson Sword Limited | N-substituted paramenthane carboxamides |
US4190643A (en) * | 1971-02-04 | 1980-02-26 | Wilkinson Sword Limited | Compositions having a physiological cooling effect |
WO1993023005A1 (en) * | 1992-05-18 | 1993-11-25 | The Procter & Gamble Company | Coolant compositions |
US6348625B1 (en) * | 2000-11-10 | 2002-02-19 | Gloria Long Anderson | Method for preparing some 1-adamantancecarboxamides |
US20050187211A1 (en) * | 2004-02-23 | 2005-08-25 | Wei Edward T. | N-arylsalkyl-carboxamide compositions and methods |
WO2006092076A2 (en) * | 2005-03-02 | 2006-09-08 | Givaudan Sa | Carboxylic acid amides provoking a cooling sensation |
Family Cites Families (44)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1179261A (en) * | 1915-10-25 | 1916-04-11 | Ralph Wymore | Wireless check-row planter. |
US3516943A (en) * | 1966-12-06 | 1970-06-23 | Ncr Co | Replacement of capsule contents by diffusion |
US4136163A (en) * | 1971-02-04 | 1979-01-23 | Wilkinson Sword Limited | P-menthane carboxamides having a physiological cooling effect |
GB1351761A (en) | 1971-02-04 | 1974-05-01 | Wilkinson Sword Ltd | Substituted p-menthane carboxamides and compositions containing them |
US4285984A (en) * | 1976-08-09 | 1981-08-25 | Givaudan Corporation | Flavoring with dialkylamino-alkylene mercaptans and sulfides |
IL83163A (en) * | 1986-07-18 | 1991-06-10 | Erba Carlo Spa | Cycloalkyl-substituted 4-pyridyl derivatives,their preparation and pharmaceutical compositions containing them |
US5009893A (en) * | 1989-07-17 | 1991-04-23 | Warner-Lambert Company | Breath-freshening edible compositions of methol and a carboxamide |
US5759599A (en) * | 1992-03-30 | 1998-06-02 | Givaudan Roure Flavors Corporation | Method of flavoring and mechanically processing foods with polymer encapsulated flavor oils |
JPH11502195A (ja) * | 1995-03-16 | 1999-02-23 | ザ、プロクター、エンド、ギャンブル、カンパニー | 清涼組成物 |
US5843466A (en) * | 1995-08-29 | 1998-12-01 | V. Mane Fils S.A. | Coolant compositions |
US6056949A (en) * | 1995-10-27 | 2000-05-02 | Givaudan Roure (International) Sa | Aromatic granulated material |
US6306818B1 (en) * | 1996-06-24 | 2001-10-23 | Givaudan Roure (International) Sa | Fragrance precursors |
DE69726446T2 (de) * | 1996-10-09 | 2004-08-26 | Givaudan S.A. | Verfahren zur herstellung eines perlförmigen nahrungsmittelzusatzes |
US6325859B1 (en) * | 1996-10-09 | 2001-12-04 | Givaudan Roure (International) Sa | Process for preparing beads as food or tobacco additive |
US6039901A (en) * | 1997-01-31 | 2000-03-21 | Givaudan Roure Flavors Corporation | Enzymatically protein encapsulating oil particles by complex coacervation |
US6045835A (en) * | 1997-10-08 | 2000-04-04 | Givaudan Roure (International) Sa | Method of encapsulating flavors and fragrances by controlled water transport into microcapsules |
US6106875A (en) | 1997-10-08 | 2000-08-22 | Givaudan Roure (International) Sa | Method of encapsulating flavors and fragrances by controlled water transport into microcapsules |
SG74666A1 (en) * | 1997-10-21 | 2000-08-22 | Givaudan Roure Int | Beta-ketoester |
SG71201A1 (en) * | 1998-04-20 | 2000-03-21 | Givaudan Roure Int | Hydroxa-methyl-hexanones |
ATE367845T1 (de) * | 1998-06-15 | 2007-08-15 | Procter & Gamble | Riechstoffzusammensetzungen |
JP2002520405A (ja) * | 1998-07-17 | 2002-07-09 | ジボーダン ルール (アンテルナシヨナル)ソシエテ アノニム | ジカルボアルコキシジオキソラン |
EP0987018A3 (en) * | 1998-08-27 | 2000-04-26 | Givaudan Roure (International) S.A. | Post-foaming shower gel |
US6108875A (en) * | 1999-05-18 | 2000-08-29 | National Molding Corp. | Lockable strap divider |
ATE254101T1 (de) * | 1999-05-28 | 2003-11-15 | Givaudan Sa | Mercaptoalkohol-verbindungen als als geschmackstoffe |
US6805893B2 (en) * | 1999-05-28 | 2004-10-19 | Givaudan Sa | Mercapto-alkanol flavor compounds |
US6689740B1 (en) * | 1999-06-15 | 2004-02-10 | Givaudan Sa | Method for preparing fragrance products |
ZA200003120B (en) * | 1999-06-30 | 2001-01-02 | Givaudan Roure Int | Encapsulation of active ingredients. |
AU7247000A (en) * | 2000-01-11 | 2001-07-19 | Givaudan Sa | Composite materials |
US6451366B1 (en) * | 2000-11-06 | 2002-09-17 | Givaudan Sa | Epoxydecenal isomers |
US6335047B1 (en) * | 2000-11-06 | 2002-01-01 | Givaudan Sa | Epoxydecenal isomers |
US20050214337A1 (en) * | 2002-02-26 | 2005-09-29 | Mcgee Thomas | Pesticidal compositions |
US20030165587A1 (en) * | 2002-02-28 | 2003-09-04 | Givaudan Sa | Production of 2-furfurylthiol in brassica seed and use of same |
EP1348423A1 (en) * | 2002-03-27 | 2003-10-01 | Givaudan SA | Fragrance compositions |
JP2005533897A (ja) * | 2002-07-25 | 2005-11-10 | ジボダン エス エー | 香り(Flavourant)化合物 |
AU2003271498A1 (en) * | 2002-10-28 | 2004-05-13 | Givaudan Sa | Coolant solutions and compositions comprising the sameitle |
US20060035008A1 (en) * | 2002-11-14 | 2006-02-16 | Givaudan Sa | Edible film containing food acid |
GB0301662D0 (en) * | 2003-01-24 | 2003-02-26 | Givaudan Sa | Improvements in or relating to organic compounds |
GB0306152D0 (en) * | 2003-03-19 | 2003-04-23 | Givaudan Sa | Method |
CN102389409B (zh) | 2003-07-02 | 2014-01-22 | 健泰科生物技术公司 | Trp-p8活性化合物和治病性治疗方法 |
US8362264B2 (en) * | 2003-08-22 | 2013-01-29 | Dendreon Corporation | Compositions and methods for the treatment of disease associated with Trp-p8 expression |
JP4786544B2 (ja) * | 2003-11-21 | 2011-10-05 | ジボダン エス エー | N置換p−メンタンカルボキサミド類 |
GB0425661D0 (en) | 2004-11-23 | 2004-12-22 | Givaudan Sa | Organic compounds |
JP2008521942A (ja) | 2004-11-29 | 2008-06-26 | ジボダン エス エー | 基材ケア製品 |
BRPI0609447A2 (pt) * | 2005-03-24 | 2010-04-06 | Givaudan Sa | compostos refrescantes |
-
2006
- 2006-08-14 EP EP06761278.8A patent/EP1917074B1/en active Active
- 2006-08-14 BR BRPI0616821-3A patent/BRPI0616821B1/pt active IP Right Grant
- 2006-08-14 JP JP2008526348A patent/JP5383191B2/ja active Active
- 2006-08-14 ES ES06761278.8T patent/ES2668361T3/es active Active
- 2006-08-14 US US11/990,103 patent/US9452982B2/en active Active
- 2006-08-14 CN CN200680029790XA patent/CN101257949B/zh active Active
- 2006-08-14 WO PCT/CH2006/000427 patent/WO2007019719A1/en active Application Filing
-
2016
- 2016-09-26 US US15/276,248 patent/US10221136B2/en active Active
-
2019
- 2019-03-01 US US16/290,300 patent/US11059783B2/en active Active
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH491111A (de) * | 1966-01-28 | 1970-05-31 | Geigy Ag J R | Verfahren zur Herstellung von neuen Amiden aliphatischer Carbonsäuren |
US4150052A (en) * | 1971-02-04 | 1979-04-17 | Wilkinson Sword Limited | N-substituted paramenthane carboxamides |
US4190643A (en) * | 1971-02-04 | 1980-02-26 | Wilkinson Sword Limited | Compositions having a physiological cooling effect |
DE2458562A1 (de) * | 1973-12-12 | 1975-06-19 | Wilkinson Sword Ltd | Verbrauchsprodukt mit physiologischer kuehlwirkung |
WO1993023005A1 (en) * | 1992-05-18 | 1993-11-25 | The Procter & Gamble Company | Coolant compositions |
US6348625B1 (en) * | 2000-11-10 | 2002-02-19 | Gloria Long Anderson | Method for preparing some 1-adamantancecarboxamides |
US20050187211A1 (en) * | 2004-02-23 | 2005-08-25 | Wei Edward T. | N-arylsalkyl-carboxamide compositions and methods |
WO2006092076A2 (en) * | 2005-03-02 | 2006-09-08 | Givaudan Sa | Carboxylic acid amides provoking a cooling sensation |
Cited By (63)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
USRE44339E1 (en) | 2003-11-21 | 2013-07-02 | Givaudan S.A. | N-substituted P-menthane carboxamides |
WO2008107137A3 (en) * | 2007-03-02 | 2009-03-26 | Givaudan Nederland Services B | Compositions comprising a physiological coolant |
WO2008107137A2 (en) * | 2007-03-02 | 2008-09-12 | Givaudan Nederland Services B.V. | Compositions comprising a physiological coolant |
US8288441B2 (en) | 2007-03-02 | 2012-10-16 | Givaudan Nederland Services B.V. | Compositions comprising a physiological coolant |
US8357318B2 (en) | 2007-05-08 | 2013-01-22 | Givaudan S.A. | Wax encapsulation |
WO2008141469A2 (en) * | 2007-05-23 | 2008-11-27 | Givaudan Sa | Butone derivatives useful as cooling agents |
US7935848B2 (en) | 2007-05-23 | 2011-05-03 | Givaudan S.A. | Butone derivatives useful as cooling agents |
WO2008141469A3 (en) * | 2007-05-23 | 2009-05-07 | Givaudan Sa | Butone derivatives useful as cooling agents |
WO2008148234A1 (en) | 2007-06-06 | 2008-12-11 | Givaudan Sa | Salt enhancement |
WO2008151460A2 (en) | 2007-06-13 | 2008-12-18 | Givaudan Sa | Cooling compounds |
US7959958B2 (en) | 2007-06-13 | 2011-06-14 | Givaudan, S.A. | Cooling compounds |
WO2009012609A1 (en) | 2007-07-23 | 2009-01-29 | Givaudan Sa | Amide addition reaction |
JP2010534209A (ja) * | 2007-07-23 | 2010-11-04 | ジボダン エス エー | アミド付加反応 |
US7880011B2 (en) | 2007-07-23 | 2011-02-01 | Givandan, S.A. | Amide addition reaction |
US8377422B2 (en) | 2007-12-07 | 2013-02-19 | Givaudan S.A. | Carboxamide derivatives having cooling properties |
US8309598B2 (en) | 2007-12-19 | 2012-11-13 | Givaudan S.A. | Cooling compounds |
WO2009115163A2 (de) * | 2008-03-20 | 2009-09-24 | Beiersdorf Ag | Kühlende kosmetische oder dermatologische zubereitungen mit einem gehalt an (1r,2s,5r)-2-isopropyl-5-methyl-n-(2-(pyridyn-2-yl)ethyl-cyclohexancarboxamid und/oder (1r,2s,5r)-n-(4-(cyanomethyl)phenyl)-2-isopropyl-5- methylcyclohexancarboxamid zu reduktion von hautrötungen |
WO2009115164A3 (de) * | 2008-03-20 | 2009-11-19 | Beiersdorf Ag | Kühlende kosmetische oder dermatologische zubereitungen mit einem gehalt an (1r,2s,5r)-2-isopropyl-5-methyl-n-(2-(pyridyn-2-yl)ethyl-cyclohexancarboxamid und/oder (1r,2s,5r)-n-(4-(cyanomethyl)phenyl)-2-isopropyl-5- methylcyclohexancarboxamid mit menthoxypropandiol |
WO2009115165A2 (de) * | 2008-03-20 | 2009-09-24 | Beiersdorf Ag | Kühlende zubereitungen für den humanen haut- und/oder schleimhautkontakt mit einem gehalt an (1r,2s,5r)-2-isopropyl-5-methyl-n-(2-(pyridin-2-yl)ethyl-cyclohexancarboxamid und/oder (1r,2s,5r)-n-(4-(cyanomethyl)-phenyl)-2-isopropyl-5-methylcyclohexancarboxamid |
US8343465B2 (en) | 2008-03-20 | 2013-01-01 | Beiersdorf Ag | Cooling cosmetic or dermatological preparations comprising (1R,2S,5R)-2-isopropyl-5-methyl-N-(2-(pyridin-2-yl)ethyl)-cyclohexane carboxamide and/or (1R,2S,5R)-N-(4-cyanomethyl-phenyl)-2-isopropyl-5-methylcyclohexane carboxamide for reducing skin reddening |
US20090306152A1 (en) * | 2008-03-20 | 2009-12-10 | Beiersdorf Ag. | Cooling cosmetic or dermatological preparations comprising (1r,2s,5r)-2-isopropyl-5-methyl-n-(2-(pyridin-2-yl)ethyl)-cyclohexane carboxamide and/or (1r,2s,5r)-n-(4-cyanomethyl-phenyl)-2-isopropyl-5-methylcyclohexane carboxamide in combination with menthoxypropanediol |
WO2009115164A2 (de) * | 2008-03-20 | 2009-09-24 | Beiersdorf Ag | Kühlende kosmetische oder dermatologische zubereitungen mit einem gehalt an (1r,2s,5r)-2-isopropyl-5-methyl-n-(2-(pyridyn-2-yl)ethyl-cyclohexancarboxamid und/oder (1r,2s,5r)-n-(4-(cyanomethyl)phenyl)-2-isopropyl-5- methylcyclohexancarboxamid mit menthoxypropandiol |
WO2009127282A1 (de) * | 2008-03-20 | 2009-10-22 | Beiersdorf Ag | Zubereitungen zur verringerung von juckreiz und anderen missempfindungen mit (1 r,2s,5r)-isopropyl-5-methyl-n(2-(pyridin-2yl)ethyl- cyclohexancarboxamid und/oder (1r,2s,5r)-n-(4-(cyanomethyl)-phenyl)-2- isopropyl-5-methylcyclohexancarboxamid |
WO2009115163A3 (de) * | 2008-03-20 | 2009-11-19 | Beiersdorf Ag | Kühlende kosmetische oder dermatologische zubereitungen mit einem gehalt an (1r,2s,5r)-2-isopropyl-5-methyl-n-(2-(pyridyn-2-yl)ethyl-cyclohexancarboxamid und/oder (1r,2s,5r)-n-(4-(cyanomethyl)phenyl)-2-isopropyl-5- methylcyclohexancarboxamid zu reduktion von hautrötungen |
WO2009115165A3 (de) * | 2008-03-20 | 2009-11-19 | Beiersdorf Ag | Kühlende zubereitungen für den humanen haut- und/oder schleimhautkontakt mit einem gehalt an (1r,2s,5r)-2-isopropyl-5-methyl-n-(2-(pyridin-2-yl)ethyl-cyclohexancarboxamid und/oder (1r,2s,5r)-n-(4-(cyanomethyl)-phenyl)-2-isopropyl-5-methylcyclohexancarboxamid |
US20120039823A1 (en) * | 2008-03-20 | 2012-02-16 | Beiersdorf Ag | Preparations for reducing itching and other paraesthesias with (1r,2s,5r)-2-isopropyl-5-methyl-n-(2-(pyridin-2-yl)ethylcyclohexanecarboxamide and/or (1r,2s,5r)-n-(4-(cyanomethyl)-phenyl)-2-isopropyl-5-methylcyclohexanecarboxamide and/or (1r,2s,5r)-n-(4-(cyanomethyl)-phenyl)-2isopropyl-5-methylcyclohexanecarboxamide |
WO2009140783A1 (en) * | 2008-05-22 | 2009-11-26 | Givaudan Sa | Cooling composition |
EP3115045A2 (de) | 2008-08-26 | 2017-01-11 | Basf Se | Nachweis und verwendung niedermolekularer modulatoren des kälte-menthol-rezeptors trpm8 |
US8710096B2 (en) | 2008-08-26 | 2014-04-29 | Basf Se | Detection and use of low molecular-weight modulators of the cold-menthol receptor TRPM8 |
US9346823B2 (en) | 2008-08-26 | 2016-05-24 | Basf Se | Detection and use of low molecular-weight modulators of the cold-menthol receptor TRPM8 |
EP3103447A1 (de) | 2008-08-26 | 2016-12-14 | Basf Se | Nachweis und verwendung niedermolekularer modulatoren des kälte-menthol-rezeptors trpm8 |
EP3698779A1 (de) | 2008-08-26 | 2020-08-26 | Basf Se | Nachweis und verwendung niedermolekularer modulatoren des kälte-menthol-rezeptors trpm8 |
WO2010076123A2 (en) | 2008-12-30 | 2010-07-08 | Unilever Nv | A non-freezing dentifrice composition |
US8664261B2 (en) | 2009-05-05 | 2014-03-04 | Givaudan S.A. | Organic compounds having cooling properties |
WO2010128026A3 (en) * | 2009-05-05 | 2011-03-31 | Givaudan Sa | Organic compounds having cooling properties |
WO2010128026A2 (en) * | 2009-05-05 | 2010-11-11 | Givaudan Sa | Organic compounds |
CN102497787A (zh) * | 2009-07-29 | 2012-06-13 | 奇华顿股份有限公司 | 有机化合物中或与之相关的改进 |
WO2011012671A1 (en) | 2009-07-29 | 2011-02-03 | Givaudan Sa | Improvements in or relating to organic compounds |
WO2011012421A1 (en) | 2009-07-29 | 2011-02-03 | Unilever Nv | A dentifrice composition comprising polyethyleneglycol and a cooling agent |
DE102010002558A1 (de) | 2009-11-20 | 2011-06-01 | Symrise Ag | Verwendung physiologischer Kühlwirkstoffe und Mittel enthaltend solche Wirkstoffe |
EP3663366A2 (de) | 2009-11-20 | 2020-06-10 | Symrise AG | Verwendung physiologischer kühlwirkstoffe und mittel enthaltend solche wirkstoffe |
WO2011061330A2 (de) | 2009-11-20 | 2011-05-26 | Symrise Ag | Verwendung physiologischer kühlwirkstoffe und mittel enthaltend solche wirkstoffe |
EP3434330A1 (en) | 2010-06-14 | 2019-01-30 | Symrise AG | A method for enhancing the cooling effect of a cooling compound |
EP2394703A1 (de) | 2010-06-14 | 2011-12-14 | Symrise AG | Kühlmischungen mit verstärkter Kühlwirkung von 5-Methyl-2-(propan-2-yl)cyclohexyl-N-ethyloxamat |
WO2010149798A2 (en) | 2010-06-14 | 2010-12-29 | Symrise Ag | Use of polyols for enhancing the cooling effect of a cooling substance and cooling mixtures having an enhanced cooling effect |
US9029415B2 (en) | 2010-06-14 | 2015-05-12 | Symrise Ag | Cooling mixtures with an enhanced cooling effect of 5-methyl-2-(propane-2-yl)cyclohexyl-N-ethyloxamate |
CN103391764A (zh) * | 2011-02-23 | 2013-11-13 | 奇华顿股份有限公司 | 有机化合物 |
WO2012113873A3 (en) * | 2011-02-23 | 2013-06-06 | Givaudan Sa | Organic compounds |
WO2012113873A2 (en) | 2011-02-23 | 2012-08-30 | Givaudan Sa | Organic compounds |
US10299999B2 (en) | 2011-02-23 | 2019-05-28 | Givaudan S.A. | Flavour composition comprising menthol and menthane carboxamides |
CN103391764B (zh) * | 2011-02-23 | 2017-04-12 | 奇华顿股份有限公司 | 有机化合物 |
CN104053429A (zh) * | 2011-07-26 | 2014-09-17 | 奇华顿股份有限公司 | 漂洗组合物 |
US9023776B2 (en) | 2011-07-26 | 2015-05-05 | Givaudan S.A. | Rinse-off compositions comprising lactoyl ethanolamine and a menthanecarboxamide compound |
WO2013014235A3 (en) * | 2011-07-26 | 2014-08-28 | Givaudan Sa | Rinse-off compositions |
WO2013014235A2 (en) | 2011-07-26 | 2013-01-31 | Givaudan Sa | Rinse-off compositions |
WO2013041621A1 (de) | 2011-09-20 | 2013-03-28 | Basf Se | Niedermolekulare modulatoren des kälte-menthol-rezeptors trpm8 und deren verwendung |
WO2019043164A1 (de) | 2017-08-31 | 2019-03-07 | Basf Se | Verwendung physiologischer kühlwirkstoffe und mittel enthaltend solche wirkstoffe |
US11434220B2 (en) | 2017-08-31 | 2022-09-06 | Basf Se | Use of physiological cooling active ingredients, and compositions comprising such active ingredients |
EP3689324A1 (de) | 2019-02-04 | 2020-08-05 | Symrise AG | Neue kühlstoffe und zubereitungen, die diese enthalten |
WO2022105986A1 (de) | 2020-11-17 | 2022-05-27 | Symrise Ag | Neue kühlstoffe und zubereitungen, die diese enthalten |
WO2023143741A1 (de) | 2022-01-28 | 2023-08-03 | Symrise Ag | Neue kühlstoffe und zubereitungen, die diese enthalten |
WO2023144326A1 (de) | 2022-01-28 | 2023-08-03 | Symrise Ag | Neue kühlstoffe und zubereitungen, die diese enthalten |
WO2022207944A2 (en) | 2022-07-11 | 2022-10-06 | Symrise Ag | Novel mixtures and uses of (2e)-3-(1,3-benzodioxol-5-yl)-n-phenyl-n-(tetrahydro-3-furanyl)-2-propenamide |
Also Published As
Publication number | Publication date |
---|---|
US11059783B2 (en) | 2021-07-13 |
JP5383191B2 (ja) | 2014-01-08 |
US10221136B2 (en) | 2019-03-05 |
BRPI0616821B1 (pt) | 2022-06-07 |
JP2009507778A (ja) | 2009-02-26 |
EP1917074B1 (en) | 2018-02-28 |
CN101257949A (zh) | 2008-09-03 |
US20190194134A1 (en) | 2019-06-27 |
US20100035938A1 (en) | 2010-02-11 |
CN101257949B (zh) | 2011-01-19 |
US20170008845A1 (en) | 2017-01-12 |
EP1917074A1 (en) | 2008-05-07 |
US9452982B2 (en) | 2016-09-27 |
ES2668361T3 (es) | 2018-05-17 |
BRPI0616821A2 (pt) | 2012-04-24 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US11059783B2 (en) | Pyridinyl cyclohexanecarboxamide cooling compounds | |
USRE44339E1 (en) | N-substituted P-menthane carboxamides | |
US7893110B2 (en) | Carboxylic acid amides provoking a cooling sensation | |
EP1860960A1 (en) | Cooling compounds | |
EP2167024B1 (en) | Cooling compounds | |
EP1940791B1 (en) | Organic compounds | |
US8377422B2 (en) | Carboxamide derivatives having cooling properties | |
EP1853565B1 (en) | Menthane carboxamide derivatives having cooling properties | |
US7935848B2 (en) | Butone derivatives useful as cooling agents | |
US20090035364A1 (en) | Para-substituted 2-alkoxyphenol compounds |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
WWE | Wipo information: entry into national phase |
Ref document number: 2006761278 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2008526348 Country of ref document: JP Ref document number: 771/CHENP/2008 Country of ref document: IN |
|
WWE | Wipo information: entry into national phase |
Ref document number: 200680029790.X Country of ref document: CN |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
WWP | Wipo information: published in national office |
Ref document number: 2006761278 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 11990103 Country of ref document: US |
|
ENP | Entry into the national phase |
Ref document number: PI0616821 Country of ref document: BR Kind code of ref document: A2 Effective date: 20080215 |